Error Sending SMTP Email - VPS Windows Unmanaged

I have a unmanaged VPS server running Windows Server 2008 r2. Right now I am configuring SMTP feature under IIS6 and set up a SMTP server. I configured DNS record as follow:

a

@

My IP Address

600 seconds

Edit

a

mail

My IP Address

600 seconds

Edit

a

mssql

My IP Address

600 seconds

Edit

cname

ftp

@

1 Hour

Edit

cname

smtp

mail.mydomain.com

1 Hour

Edit

cname

www

@

1 Hour

Edit

cname

_domainconnect

_domainconnect.gd.domaincontrol.com

1 Hour

Edit

mx

@

mail.mydomain.com (Priority: 10)

1 Hour

Edit

srv

_autodiscover._tcp.@

0 0 443 autodiscover.secureserver.net

1 Hour

Edit

srv

_smtp._tcp.@

0 0 25 mail.mydomain.com

1 Hour

Edit

ns

@

pdns07.domaincontrol.com

1 Hour

ns

@

pdns08.domaincontrol.com

1 Hour

And I have mail.mydomain.com as Fully Qualified Domain Name under SMTP server properties, Used my IP address and port 25. I also set access control and outbound security to anonymous, connection control and relay restrictions are only given to 127.0.0.1.

But I tried SMTPdiag to test SMTP connection and it fails to connect the destination smtp server as follow:

PS C:\smtpdiag> ./smtpdiag example@mydomain.com myemail@gmail.com

Searching for Exchange external DNS settings.Computer name is Somethin.Failed to connect to the domain controller. Error: 8007054b

Checking MX servers listed for something@gmail.comConnecting to gmail-smtp-in.l.google.com [74.125.28.27] on port 25.Connecting to the server failed. Error: 10060Failed to submit mail to gmail-smtp-in.l.google.com.Connecting to alt1.gmail-smtp-in.l.google.com [74.125.132.26] on port 25.Connecting to the server failed. Error: 10060Failed to submit mail to alt1.gmail-smtp-in.l.google.com.Connecting to alt2.gmail-smtp-in.l.google.com [173.194.219.27] on port 25.Connecting to the server failed. Error: 10060Failed to submit mail to alt2.gmail-smtp-in.l.google.com.Connecting to alt3.gmail-smtp-in.l.google.com [173.194.68.27] on port 25.Connecting to the server failed. Error: 10060Failed to submit mail to alt3.gmail-smtp-in.l.google.com.Connecting to alt4.gmail-smtp-in.l.google.com [173.194.210.26] on port 25.Connecting to the server failed. Error: 10060Failed to submit mail to alt4.gmail-smtp-in.l.google.com.

I am wondering what's wrong with the configuration and someone pleas can help me. Thank you for your time.

Re: Error Sending SMTP Email - VPS Windows Unmanaged

Hi @jpablo, support team told me server is not supporting direct smtp delivery and I have to use smtp relay server to deliver. Also, newer server is using dedrelay.secureserver.net as relay. It is working now. Thank you for your help.

Re: Error Sending SMTP Email - VPS Windows Unmanaged

I know this is already solved but there is a key piece of information here that may help someone in the future.

As ngeforce noted, the relay server is dedrelay.secureserver.net, NOT relay-hosting.secureserver.net as stated in GoDaddy's documentation (https://uk.godaddy.com/help/send-email-using-systemnetmail-19291). I'll lost quite a few hours testing all kinds of parameters trying to send emails from a VPS using ASP.Net and finally came across this alternate or newer relay server. Thanks ngeforce!

Here are the parameters I'm using and that are working for me in case anyone is trying to programmatically send emails.